Caroline helps someone she once bullied; Annie finds companionship in a parrot; Del finds his girlfriend's height intimidating.
An unexpected guest interrupts Caroline and Randy's wedding.
Caroline and Richard prepare to wed, then he learns he will be a father.
Richard gets locked up at the time he must answer Caroline's marriage ultimatum.
Randy surprises Caroline with a visit, and they end up stuck in a subway tunnel.
Caroline learns an ex-boyfriend will be her new tenant.
The gang visits Caroline's parents who tell her they are selling their house.
Caroline imagines what her life would be like if she wasn't a cartoonist.
Caroline takes hapless Charlie under her wing after Del is forced to fire him.
Caroline and Del get mixed results when each mentors a young person at work.
Richard allows Reg to become a house guest; Annie and Del join a health club.
After mocking Caroline for her spirit, her friends take her to Christmasville.
An aunt offers Richard $5,000 to have a bar mitzvah; Del's costly suits are too tight.
Caroline dreams of life with a larger bosom when Annie decides to get implants.
Caroline angers a temperamental soprano when she invites pals to the opera.
Caroline and Richard decide to consummate their relationship.
Caroline accidentally circulates Richard's divorce papers in the interoffice mail.
Caroline and Richard's first date is a fright; Del organizes the office Halloween party.
Annie dates her dry cleaner; Del's focus group discusses Caroline's cards.
Manager Plum banishes Caroline and Richard to a damp, dark basement office.
Richard's father-in-law cleans him out, forcing him to sleep in Caroline's office.
Unexpected visitors interrupt Caroline and Richard as they prepare for romance.
Caroline tells Richard she thinks Julia is having an affair with a bullfighter during her Spanish holiday; guest Liz Torres.
A troubled patient (Garry Shandling) tracks down Dr. Leslie at Caroline's.
An inheritance allows Richard to paint full time, forcing Caroline to seek a new colorist; Richard and Sofia see a marriage counselor; guest Garry Shandling.
Tabloid TV looks for a story when a Worley sandwich is renamed after 'Caroline in the City.'
Caroline fears for Richard's life when he accompanies his father-in-law on a trip.
Caroline (Lea Thompson) helps Angie (guest star Candice Azzara); Del and Charlie's (Eric Lutes, Andy Lauer) fictional gay relationship presents problems for Del's new love interest (guest star Angie Everhart).
Caroline and her mother are featured in a magazine article.
Insulted by a cabbie (guest star Saverio Guerra), Caroline appeals to the travel commission; Richard (Malcolm Gets) joins a cybercafe; Annie's (Amy Pietz) appointment.
Richard inadvertently causes a rift between Caroline and her new beau, Trevor.
Mysteriously, Caroline and Julia each experience life as the other.
Caroline tries to reassure Del when he learns he has a 10-year-old daughter.
Richard helps Caroline study when a TV quiz show taps her as a contestant.
Guests wind up in the ER when Caroline throws a party for Richard and Julia.
Caroline spends Christmas with Del's family; stranded Annie and Richard bond.
A crazy car dealer (David Leisure) helps Richard earn money for a gift.
A councilman, inspired by Caroline's comic strip, seeks her endorsement.
Richard accuses his former piano teacher, Marvin Hamlisch, of plagiarism.
Richard can't find his cursed family wedding ring; Annie debuts her cabaret act.
Annie tells her old voice teacher (Harriet Sansom Harris) she's still in 'Cats.'
Caroline ponders motherhood when a friend asks her to be an egg donor.
Richard sets up obstacles when Sofia arranges a blind date for Caroline.
Caroline's neighbors resent her honesty with the cable-TV company.
Caroline's date with a novelist turns into a disaster.
Caroline realizes stress over Richard is causing the constant aching in her neck.
Richard's love Sofia has news for Caroline; Annie returns from Los Angeles.
Caroline considers telling Richard her true feelings for him.
Caroline poses as Richard's wife to impress his ex-flame (Sofia Milos).
Caroline is set to appear on 'The Tonight Show'; Richard's mother reveals his father's identity.
Caroline hires a mediator to confront her neglectful building superintendent.
Caroline is upset when a paper cancels her strip.
Caroline caters to her demanding, elderly neighbor (Marilyn Cooper).
A prospective buyer for Caroline's work misinterprets her charm.
Caroline braves an evening alone on the town; guest Helen Slater.
Caroline and Annie both find men on their girls-only ski trip.
Caroline tells an art columnist that Richard is dead to boost the value of his art.
Richard gets a chance to score big money at a Knicks game; guest French Stewart.
Richard (Malcolm Gets) misunderstands a wealthy socialite's (guest star Ann Magnuson) interest; Caroline (Lea Thompson) begins reading to an elderly woman (guest star Rose Marie).
Annie's sister (Mackenzie Phillips) finds Richard's love letter to Caroline.
Caroline turns to Richard when Joe's old girlfriend takes shelter at his place.
Caroline (Lea Thompson) spends a night locked in the laundry with a homeless man (guest star Harry Groener).
Annie's mother (Candice Azzara) unexpectedly wants to move in with her.
Veterinarian Joe recommends Caroline take her cat to a therapist.
Caroline reunites Richard with his father (Judd Hirsch), a vaudevillian comic.
Annie does research for her audition for 'Victor/Victoria.'
Gentile Del falls for a woman (Rena Sofer) who dates only Jewish men.
The city commissions Richard to paint a mural in a dangerous location.
When Joe declares his love for Caroline, she decides to date an older man.
Annie misconstrues an IRS auditor's demeanor; guest David Hyde Pierce.
Caroline offers Richard his old job; pregnant Vicki goes into early labor.
Romantic sparks fly between Caroline and a young veterinarian.
The prospect of an afternoon tryst lands Caroline in hot water.
Chaos reigns at the wedding; guest Michael McKean.
Stress tests friends when Caroline entrusts Annie with maid-of-honor duties.
Richard tries to resolve issues with his jet-setting mother (Elizabeth Ashley); guest John Ratzenberger.
Caroline's agent (Meshach Taylor) lands her a cereal-company deal; guest star Vicki Lewis.
Caroline and Annie become movie extras; guest Robby Benson; John Landis.
Del and Caroline (Eric Lutes, Lea Thompson) run into his bitter ex-wife (guest star Joely Fisher) while on a weekend trip.
A wealthy man commissions Caroline to draw a mural for his son.
Del's proposal to Caroline prompts Richard to look for work; guest Sharon Lawrence.
Caroline mistakenly thinks she has found the perfect man (Dan Cortese).
Caroline and Richard seek a solution to sharing their work space; a guilt-ridden Del attends an employee's funeral.
Caroline visits her relatives when her hometown dedicates a park in her name.
Richard sets Caroline up on a date with a married man.
Caroline looks for a hidden meaning behind Del's lavish Christmas gift.
Caroline and Del reconsider their relationship while planning a Paris getaway.
Caroline and Del go out with Amy and an ex-convict.
Caroline's cartoon merits a balloon in the Thanksgiving parade; guest Florence Henderson; Mike Burger; Maty Monfort.
Caroline's (Lea Thompson) favorite aunt (guest star Jean Stapleton) arranges a date that makes Del (Eric Lutes) jealous.
Caroline meets Del's parents; guests Matthew Perry; Jonathan Silverman.
The bank camera captures Caroline's awkward moment at an ATM.
While Caroline nurses a back injury, Del and Richard race to finish her cartoon.
Richard displays his paintings in a prestigious gallery; guest Dan Butler.
When a mugger takes Richard's portfolio, Caroline has to recreate her drawings.
The life of a New York cartoonist winds up in her comic strip.